thioridazine   

GtoPdb Ligand ID: 100

Synonyms: Mellaril® | thioridazin | TP-21
thioridazine is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: Marketed formulations may contain thioridazine hydrochloride (PubChem CID 66062).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 57.08
Molecular weight 370.15
XLogP 5.94
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CSc1ccc2c(c1)N(CCC1CCCCN1C)c1c(S2)cccc1
Isomeric SMILES CSc1ccc2c(c1)N(CCC1CCCCN1C)c1c(S2)cccc1
InChI InChI=1S/C21H26N2S2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
InChI Key KLBQZWRITKRQQV-UHFFFAOYSA-N
References
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Inverse agonist activity of atypical antipsychotic drugs at human 5-hydroxytryptamine2C receptors.
J. Pharmacol. Exp. Ther., 295 (1): 226-32. [PMID:10991983]
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Inhibition by various antipsychotic drugs of the G-protein-activated inwardly rectifying K(+) (GIRK) channels expressed in xenopus oocytes.
Br. J. Pharmacol., 129 (8): 1716-22. [PMID:10780978]
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A comparison of the receptor binding and HERG channel affinities for a series of antipsychotic drugs.
Eur. J. Pharmacol., 450 (1): 37-41. [PMID:12176106]
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H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs.
Neuropsychopharmacology, 28 (3): 519-26. [PMID:12629531]
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Agonist and antagonist actions of antipsychotic agents at 5-HT1A receptors: a [35S]GTPgammaS binding study.
Eur. J. Pharmacol., 355 (2-3): 245-56. [PMID:9760039]
6. Purohit A, Smith C, Herrick-Davis K, Teitler M. (2005)
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs.
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7. Roth BL, Craigo SC, Choudhary MS, Uluer A, Monsma Jr FJ, Shen Y, Meltzer HY, Sibley DR. (1994)
Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors.
J. Pharmacol. Exp. Ther., 268 (3): 1403-10. [PMID:7908055]
8. Sunahara RK, Guan HC, O'Dowd BF, Seeman P, Laurier LG, Ng G, George SR, Torchia J, Van Tol HH, Niznik HB. (1991)
Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1.
Nature, 350 (6319): 614-9. [PMID:1826762]